Phenacylamine derivatives, process for their production and pesticides containing them

ABSTRACT

The present invention relates to a phenacylamine derivative of the formula (I) or a salt thereof: 
                         
wherein A is alkyl, cycloalkyl, phenyl which may be substituted by Y, pyridyl which may be substituted by Y, or pyrazolyl which may be substituted by Y, R 1  and R 2  are each alkyl, or R 1  and R 2  may together form a 3- to 6-membered saturated carbocycle, R 3  is hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl or COR 4 , X is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted by Y, phenoxy which may be substituted by Y, benzyloxy which may be substituted by Y, or pyridyloxy which may be substituted by Y, and n is an integer of from 0 to 5.

TECHNICAL FIELD

The present invention relates to novel phenacylamine derivatives usefulas active ingredients for pesticides.

BACKGROUND ART

JP-B-48-18222 discloses a process for producing acylaminoketonederivatives, but there is no specific disclosure relating tophenacylamine derivatives of the formula (I) given hereinafter. Further,the same publication discloses nothing about usefulness as pesticideswhich will be described hereinafter.

Over the years, a number of pesticides have been used, but many of themhave various problems such that the effects are inadequate, their use isrestricted as the pests have acquired resistance, they have hightoxicity against human, animal, fish, etc., and their residual effectsdisturb the ecological system. Accordingly, it is desired to developnovel pesticides having high safety without such drawbacks.

Further, parasites on animals are parasitic on the body surfaces,stomachs, intestinal tracts, lungs, hearts, livers, blood vessels,subcutis and lymphatic tissues of domestic animals or companion animalsand thus cause various animal diseases, such as anemia, malnutrition,asthenia, weight loss or disorders of intestinal tract walls, organs orother tissues. Accordingly, it is desired to control such parasites.

DISCLOSURE OF THE INVENTION

The present inventors have conducted various studies on phenacylaminederivatives to find a superior pesticide. As a result, it has been foundthat novel phenacylamine derivatives and their salts have very highcontrolling effects against pests at low doses, and they show nosubstantial adverse effects against mammals, fish, etc. The presentinvention has been accomplished on the basis of this discovery.

That is, the present invention provides a phenacylamine derivative ofthe formula (I) or a salt thereof:

wherein A is alkyl, cycloalkyl, phenyl which may be substituted by Y,pyridyl which may be substituted by Y, or pyrazolyl which may besubstituted by Y, R₁ and R₂ are each alkyl, or R₁ and R₂ may togetherform a 3- to 6-membered saturated carbocycle, R₃ is hydrogen, alkyl,alkoxyalkyl, alkylthioalkyl or COR₄, R₄ is alkyl or alkoxy, X ishalogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl,alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy,haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio,alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano,phenyl which may be substituted by Y, phenoxy which may be substitutedby Y, benzyloxy which may be substituted by Y, or pyridyloxy which maybe substituted by Y, Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy,alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro or cyano,n is an integer of from 0 to 5, and when n is 2 or more, a plurality ofX may be the same or different, provided that a case where A isunsubstituted phenyl, R₁ and R₂ are each methyl or together form a6-membered saturated carbocycle, R₃ is hydrogen, and n is 0, isexcluded; a process for its production; and a pesticide containing it.

Now, the present invention will be described in detail with reference tothe preferred embodiments.

The alkyl or alkyl moiety in A, R₁, R₂, R₃, R₄, X and Y may be linear orbranched one having from 1 to 6 carbon atoms, such as methyl, ethyl,propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl.

The cycloalkyl in A may be one having from 3 to 6 carbon atoms, such ascyclopropyl, cyclopentyl or cyclohexyl.

The alkenyl or alkenyl moiety in X may be linear or branched one havingfrom 2 to 7 carbon atoms, such as vinyl, 1-propenyl, allyl, isopropenyl,1-butenyl, 1,3-butadienyl, 1-hexenyl or 1-heptenyl. Further, the alkynylor alkynyl moiety in X may be linear or branched one having from 2 to 7carbon atoms, such as ethynyl, 2-butynyl, 2-pentynyl, 3-hexynyl or4-dimethyl-2-pentynyl.

The number of substituents Y in the phenyl which may be substituted byY, the pyridyl which may be substituted Y and the pyrazolyl which may besubstituted by Y, in A, and the phenyl which may be substituted by Y,the phenoxy which may be substituted by Y, the benzyloxy which may besubstituted by Y and the pyridyloxy which may be substituted by Y, in X,may be one or more, and in the case of more than one, such substituentsmay be the same or different.

The halogen in X and Y or the halogen as a substituent may be an atom offluorine, chlorine, bromine or iodine. The number of halogens assubstituents may be one or more, and in a case where it is more thanone, the respective halogens may be the same or different. Further, suchhalogens may be substituted at any position.

The salt of the phenacylamine derivative of the above formula (I) may beany salt so long as it is agriculturally acceptable. For example, it maybe an alkali metal salt such as a sodium salt or a potassium salt; analkaline earth metal salt such as a magnesium salt or a calcium salt; anammonium salt such as a dimethylamine salt or a triethylamine salt; aninorganic salt such as a hydrochloride, a perchlorate, a sulfate or anitrate; or an organic salt such as an acetate or a methanesulfonate.

The phenacylamine derivative of the above formula (I) has opticalisomers, and the present invention includes various isomers and mixturesof such isomers.

The phenacylamine derivative of the above formula (I) or a salt thereof(hereinafter referred to simply as the compound of the presentinvention) can be produced by the following reaction (A) or (B), or by ausual process for producing a salt.

In the reaction (A), A, R₁, R₂, X and n are as defined above. Z ishydroxy, alkoxy or halogen, and the halogen may be an atom of fluorine,chlorine, bromine or iodine.

Reaction (A) is carried out usually in the presence of a base and asolvent.

The base may be one or more suitably selected from e.g. an alkali metalsuch as sodium or potassium; an alkali metal alcoholate such as sodiummethylate, sodium ethylate or potassium tertiary butoxide; a carbonatesuch as sodium carbonate or potassium carbonate; a bicarbonate such assodium bicarbonate or potassium bicarbonate; a metal hydroxide such assodium hydroxide or potassium hydroxide; a metal hydride such as sodiumhydride or potassium hydride; an amine such as monomethylamine,dimethylamine or triethylamine; and a pyridine such as pyridine or4-dimethylaminopyridine. The base is used in an amount of from 1 to 3mols, preferably from 1 to 2 mols, per mol of the compound of theformula (II).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran or diethyl ether; an ester such as methyl acetate orethyl acetate; a polar aprotic solvent such as dimethyl sulfoxide,sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone orpyridine; a nitrile such as acetonitrile, propionitrile or acrylonitrileand a ketone such as acetone or methyl ethyl ketone.

Reaction (A) is carried out, if necessary, in the presence of adehydration condensation agent. The dehydration condensation agent may,for example, be N,N′-dicyclohexylcarbodiimide.

The reaction temperature for reaction (A) is usually from 0 to 100° C.,preferably from 0 to 50° C., and the reaction time is usually from 0.5to 48 hours, preferably from 1 to 24 hours.

In reaction (B), A, R₁, R₂, X and n are as defined above, and R₃′ isalkyl, alkoxyalkyl, alkylthioalkyl or COR₄ (wherein R₄ is as definedabove), and W is halogen, and the halogen may be an atom of fluorine,chlorine, bromine or iodine.

Reaction (B) is carried out usually in the presence of a base and asolvent.

The base may be one or more suitably selected from e.g. an alkali metalsuch as sodium or potassium; an alkali metal alcoholate such as sodiummethylate, sodium ethylate or potassium tertiary butoxide; a carbonatesuch as sodium carbonate or potassium carbonate; a bicarbonate such assodium bicarbonate or potassium bicarbonate; a metal hydroxide such assodium hydroxide or potassium hydroxide; a metal hydride such as sodiumhydride or potassium hydride; an amine such as monomethylamine,dimethylamine or triethylamine; and a pyridine such as pyridine or4-dimethylaminopyridine. The base is used in an amount of from 1 to 3mols, preferably from 1 to 1.5 mols, per mol of the compound of theformula (I-1).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran or diethyl ether; an ester such as methyl acetate orethyl acetate; a polar aprotic solvent such as dimethyl sulfoxide,sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone orpyridine; a nitrile such as acetonitrile, propionitrile oracrylonitrile; and a ketone such as acetone or methyl ethyl ketone.

The reaction temperature for reaction (B) is usually from 0 to 100° C.,preferably from 0 to 50° C., and the reaction time is usually from 1 to300 hours, preferably from 1 to 150 hours.

The compound of the formula (II) to be used in the above reaction (A) isnovel and can be produced by the following reaction (C) or (D).

In reaction (C) R₁, R₂, X and n are as defined above. In reaction (C), asalt of the compound (II) can be produced by after treatment of thereaction or in accordance with a usual reaction for forming a salt.

Reaction (C) is carried out usually in the presence of an oxidizingagent and a solvent.

The oxidizing agent may, for example, be potassium ferricyanide. Theoxidizing agent is used in an amount of from 1 to 10 mols, preferablyfrom 1 to 5 mols, per mol of the compound of the formula (V).

The solvent may be any solvent so long as it is inert to the reaction.For example, it may be one or more suitably selected from e.g. an ethersuch as dioxane, tetrahydrofuran or diethyl ether; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; a ketone such as acetone or methyl ethylketone; and water.

The reaction temperature for reaction (C) is usually from 20 to 150° C.,preferably from 50 to 100° C. The reaction time is usually from 0.5 to30 hours, preferably from 1 to 20 hours.

In reaction (D), R₁, R₂, X and n are as defined above. In reaction (D),a salt of the compound (II) can be produced by after treatment of thereaction or in accordance with a usual reaction for forming a salt.

The cyclization reaction in reaction (D) is carried out usually in thepresence of a base and a solvent.

The base may be one or more suitably selected from e.g. an alkali metalsuch as sodium or potassium; an alkali metal alcoholate such as sodiummethylate, sodium ethylate or potassium tert-butoxide; and a metalhydride such as sodium hydride or potassium hydride. The base is used inan amount of from 1 to 3 mols, preferably from 1 to 1.5 mols per mol ofthe compound of the formula (VI).

The solvent may be any solvent so long as it is inert to the reaction.For example, it may be one or more suitably selected from e.g. anaromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene;an ether such as dioxane, tetrahydrofuran or diethyl ether; an alcoholsuch as methanol, ethanol, propanol or tert-butanol; and a nitrile suchas acetonitrile, propionitrile or acrylonitrile.

The reaction temperature for the cyclization reaction in reaction (D) isusually from 0 to 150° C., preferably from 30 to 100° C. The reactiontime is usually from 0.5 to 24 hours, preferably from 1 to 12 hours.

The hydrolytic reaction in reaction (D) may be carried out in accordancewith a common hydrolytic reaction and is carried out usually in thepresence of an acid or base and a solvent.

The acid may, for example, be hydrogen chloride or sulfuric acid. Thebase may, for example, be a metal hydroxide such as sodium hydroxide orpotassium hydroxide.

The solvent may be any solvent so long as it is inert to the reaction.For example, it may be one or more suitably selected e.g. an alcoholsuch as methanol, ethanol, propanol or tert-butanol; a nitrile such asacetonitrile, propionitrile or acrylonitrile; a ketone such as acetoneor methyl ethyl ketone; and water.

The reaction temperature for the hydrolytic reaction in reaction (D) isusually from 0 to 100° C., preferably from 20 to 80° C. The reactiontime is usually from 0.1 to 12 hours, preferably from 0.1 to 1 hour.

The compound of the formula (VI) to be used in the above reaction (D) isnovel and can be produced by the following reaction (E).

In reaction (E), R₁, R₂, X and n are as defined above.

Reaction (E) may be carried out, if necessary, in the presence of asolvent. The solvent may be any solvent so long as it is inert to thereaction, and for example, it may be one or more suitably selected frome.g. an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,chloroform, dichloromethane, dichloroethane, trichloroethane, hexane orcyclohexane; an ether such as dioxane, tetrahydrofuran or diethyl ether;an ester such as methyl acetate or ethyl acetate; an alcohol such asmethanol, ethanol, propanol or tert-butanol; a nitrile such asacetonitrile, propionitrile or acrylonitrile; and a ketone such asacetone or methyl ethyl ketone.

Methyl iodide in reaction (E) is used in an amount of from 1 to 10 mols,preferably from 1 to 3 mols, per mol of the compound of the formula(VII). Further, if used excessively, methyl iodide may serve also as asolvent.

The reaction temperature for reaction (E) is usually from 0 to 100° C.,preferably from 10 to 50° C. The reaction time is usually from 0.5 to 48hours, preferably from 1 to 24 hours.

The compound of the formula (VII) to be used in the above reaction (E)is novel and can be produced by the following reaction (F).

In reaction (F), R₁, R₂, X and n are as defined above.

Reaction (F) can be carried out in accordance with a common hydrazonesynthetic reaction and, if necessary, in the presence of a dehydratingagent and/or a catalyst.

As the dehydrating agent, molecular sieve may, for example, bementioned. The dehydrating agent may be used usually from 1 to 30 times,preferably from 5 to 10 times relative to the weight of the compound ofthe formula (V).

The catalyst may, for example, be titanium tetrachloride.

Dimethylhydrazine for reaction (F) is used usually in an amount of from1 to 30 mols, preferably from 5 to 10 mols, per mol of the compound ofthe formula (V).

The reaction temperature for reaction (F) is usually from 20 to 150° C.,preferably from 50 to 120° C. The reaction time is usually from 5 to 200hours, preferably from 24 to 120 hours.

Preferred embodiments of pesticides containing the compounds of thepresent invention will now be described.

The pesticides containing the compounds of the present invention areparticularly useful as an insecticide, a miticide, a nematicide and asoil pesticide, and they are effective for controlling plant parasiticmites such as two-spotted spider mite (Tetranychus urticae), carminespider mite (Tetranychus cinnabarinus), kanzawa spider mite (Tetranychuskanzawai), citrus red mite (Panonychus citri), European red mite(Panonychus ulmi), broad mite (Polyphagotarsonemus latus), pink citrusrust mite (Aculops pelekassi) and bulb mite (Rhizoglyphus echinopus);aphids such as green peach aphid (Myzus persicae) and cotton aphid(Aphis gossypii); agricultural insect pests such as diamondback moth(Plutella xylostella), cabbage armyworm (Mamestra brassicae), commoncutworm (Spodoptera litura), codling moth (Laspeyresia pomonella),bollworm (Heliothis zea), tobacco budworm (Heliothis virescens), gypsymoth (Lymantria dispar), rice leafroller (Cnaphalocrocis medinalis),Adoxophyes sp., colorado potato beetle (Leptinotarsa decemlineata),cucurbit leaf beetle (Aulacophora femoralis), boll weevil (Anthonomusgrandis), planthoppers, leafhoppers, scales, bugs, whiteflies, thrips,grasshoppers, anthomyiid flies, scarabs, black cutworm (Agrotisipsilon), cutworm (Agrotis segetum) and ants; plant parasitic nematodessuch as root-knot nematodes, cyst nematodes, root-lesion nematodes, ricewhite-tip nematode (Aphelenchoides besseyi), strawberry bud nematode(Nothotylenchus acris), pine wood nematode (Bursaphelenchus lignicolus);gastropods such as slugs and snails; soil pests such as isopods such aspillbugs (Armadilidium vulgare) and pillbugs (Porcellio scaber);hygienic insect pests such as tropical rat mite (Ornithonyssus bacoti),cockroachs, housefly (Musca domestica) and house mosquito (Culexpipiens); stored grain insect pests such as angoumois grai moth(Sitotroga cerealella), adzuki bean weevil (Callosobruchus chinensis),red flour beetle (Tribolium castaneum) and mealworms; household goodsinsect pests such as casemaking clothes moth (Tinea pellionella), blackcarpet beetle (Anthrenus scrophularidae) and subterranean termites;domestic mites such as mold mite (Tyrophagus putrescentiae),Dermatophagoides farinae and Chelacaropsis moorei. Among them, thepesticides containing the compounds of the present invention areparticularly effective for controlling agricultural insect pests, plantparasitic nematodes or the like. Further, they are effective againstinsect pests having acquired resistance to organophosphorus, carbamateand/or synthetic pyrethroid insecticides. Moreover, the compounds of thepresent invention have excellent systemic properties, and by theapplication of the compounds of the present invention to solidtreatment, not only noxious insects, noxious mites, noxious nematodes,noxious gastropods and noxious isopods in soil but also foliage pestscan be controlled.

Another preferred embodiments of the pesticides containing compounds ofthe present invention may be agricultural and horticultural pesticideswhich collectively control the above-mentioned plant parasitic mites,agricultural insect pests, plant parasitic nematodes, gastropods andsoil pests.

The pesticide containing the compound of the present invention, isusually formulated by mixing the compound with various agriculturaladjuvants and used in the form of a formulation such as a dust,granules, water-dispersible granules, a wettable powder, a water-basedsuspension concentrate, an oil-based suspension concentrate, watersoluble granules, an emulsifiable concentrate, a soluble concentrate, apaste, an aerosol or an ultra low-volume formulation. However, so longas it is suitable for the purpose of the present invention, it may beformulated into any type of formulation which is commonly used in thisfield. Such agricultural adjuvants include solid carriers such asdiatomaceous earth, slaked lime, calcium carbonate, talc, white carbon,kaoline, bentonite, a mixture of kaolinite and sericite, clay, sodiumcarbonate, sodium bicarbonate, mirabilite, zeolite and starch; solventssuch as water, toluene, xylene, solvent naphtha, dioxane, acetone,isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane,dimethylsulfoxide, dimethylformamide, dimethylacetamide,N-methyl-2-pyrrolidone, and alcohol; anionic surfactants and spreaderssuch as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, adialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acidester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ethersulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, analkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, analkyldiphenyl ether disulfonate, a polystyrene sulfonate, a salt ofalkylphosphoric acid ester, an alkylaryl phosphate, a styrylarylphosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, apolyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylenealkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl etherphosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester,and a salt of a condensate of naphthalene sulfonate with formalin;nonionic surfactants and spreaders such as a sorbitan fatty acid ester,a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acidalcohol polyglycol ether, acetylene glycol, acetylene alcohol, anoxyalkylene block polymer, a polyoxyethylene alkyl ether, apolyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, apolyoxyethylene glycol alkyl ether, a polyoxyethylene fatty acid ester,a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerinfatty acid ester, a polyoxyethylene hydrogenated castor oil, and apolyoxypropylene fatty acid ester; and vegetable and mineral oils suchas olive oil, kapok oil, castor oil, palm oil, camellia oil, coconutoil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil,soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffins.Such adjuvants may be selected for use among those known in this field,so long as the purpose of the present invention can thereby beaccomplished. Further, various additives which are commonly used, suchas a filler, a thickener, an anti-settling agent, an anti-freezingagent, a dispersion stabilizer, a phytotoxicity reducing agent, and ananti-mold agent, may also be employed.

The weight ratio of the compound of the present invention to the variousagricultural adjuvants is usually from 0.001:99.999 to 95:5, preferablyfrom 0.005:99.995 to 90:10.

In the actual application of such a formulation, it may be used as itis, or may be diluted to a predetermined concentration with a diluentsuch as water, and various spreaders may be added thereto, as the caserequires.

The application of the pesticide containing the compound of the presentinvention can not generally be defined, as it varies depending upon theweather conditions, the type of the formulation, the application season,the application site or the types or degree of outbreak of the pestinsects. However, it is usually applied in a concentration of the activeingredient being from 0.05 to 800,000 ppm, preferably from 0.5 to500,000 ppm, and the dose per unit area is such that the compound of thepresent invention is from 0.05 to 50,000 g, preferably from 1 to 30,000g, per hectare. Further, agricultural and horticultural pesticides asanother preferred embodiment of pesticides containing the compounds ofthe present invention may be applied in accordance with theabove-described application of pesticides. The present inventionincludes such a method for controlling pests, particularly forcontrolling agricultural insect pests or plant parasitic nematodes bysuch applications.

Various formulations of pesticides containing the compounds of thepresent invention or their diluted compositions may be applied byconventional methods for application which are commonly employed, suchas spraying (e.g. spraying, jetting, misting, atomizing, powder or grainscattering or dispersing in water), soil application (e.g. mixing ordrenching), surface application (e.g. coating, powdering or covering) orimpregnation to obtain poisonous feed. Further, it is possible to feeddomestic animals with a food containing the above active ingredient andto control the outbreak or growth of pests, particularly insect pests,with their excrements. Furthermore, the active ingredient may also beapplied by a so-called ultra low-volume application method. In thismethod, the composition may be composed of 100% of the activeingredient.

Further, the pesticides containing compounds of the present inventionmay be mixed with or may be used in combination with other agriculturalchemicals, fertilizers or phytotoxicity-reducing agents, wherebysynergistic effects or activities may sometimes be obtained. Such otheragricultural chemicals include, for example, a herbicide, aninsecticide, a miticide, a nematicide, a soil pesticide, a fungicide, anantivirus agent, an attractant, an antibiotic, a plant hormone and aplant growth regulating agent. Especially, with a mixed pesticide havinga compound of the present invention mixed with or used in combinationwith one or more active compounds of other agricultural chemicals, theapplication range, the application time, the pesticidal activities, etc.may be improved to preferred directions. The compound of the presentinvention and the active compounds of other agricultural chemicals mayseparately be formulated so that they may be mixed for use at the timeof application, or they may be formulated together. The presentinvention includes such a mixed pesticidal composition.

The mixing ratio of the compound of the present invention to the activecompounds of other agricultural chemicals can not generally be defined,since it varies depending upon the weather conditions, the types offormulations, the application time, the application site, the types ordegree of outbreak of insect pests, etc., but it is usually within arange of from 1:300 to 300:1, preferably from 1:100 to 100:1, by weight.Further, the dose for the application is such that the total amount ofthe active compounds is from 0.1 to 50,000 g, preferably from 1 to30,000 g, per hectare. The present invention includes a method forcontrolling pests by an application of such a mixed pesticidecomposition.

The active compounds of insect pest control agents such as insecticides,miticides, nematicides or soil pesticides in the above-mentioned otheragricultural chemicals, include, for example, (by common names, some ofthem are still in an application stage) organic phosphate compounds suchas Profenofos, Dichlorvos, Fenamiphos, Fenitrothion, EPN, Diazinon,Chlorpyrifos-methyl, Acephate, Prothiofos, Fosthiazate, Phosphocarb,Cadusafos, and Disulfoton; carbamate compounds such as Carbaryl,Propoxur, Aldicarb, Carbofuran, Thiodicarb, Methomyl, Oxamyl,Ethiofencarb, Pirimicarb, Fenobucarb, Carbosulfan, and Benfuracarb;nereistoxin derivatives such as Cartap, and Thiocyclam; organic chlorinecompounds such as Dicofol, and Tetradifon; organometallic compounds suchas Fenbutatin Oxide; pyrethroid compounds such as Fenvalerate,Permethrin, Cypermethrin, Deltamethrin, Cyhalothrin, Tefluthrin, andEthofenprox; benzoylurea compounds such as Diflubenzuron,Chlorfluazuron, Teflubenzuron, and Flufenoxuron; juvenile hormone-likecompounds such as Methoprene; pyridazinone compounds such as Pyridaben;pyrazole compounds such as Fenpyroximate, Fipronil, Tebufenpyrad,Ethiprole, and Tolfenpyrad; neonicotinoids such as Imidacloprid,Nitenpyram, Acetamiprid, Thiacloprid, Thiamethoxam, Clothianidin, andDinotefuran; hydrazine compounds such as Tebufenozide, Methoxyfenozide,and Chromafenozide; dinitro compounds; organic sulfur compounds; ureacompounds; triazine compounds; hydrazone compounds; and other compounds,such as Buprofezin, Hexythiazox, Amitraz, Chlordimeform, Silafluofen,Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indoxacarb,Acequinocyl, Etoxazole, Cyromazin, and 1,3-dichloropropene. Further, BTagents, microbial agricultural chemicals such as insect viruses, orantibiotics such as Avermectin, Milbemectin and Spinosad, may be used inadmixture or in combination.

The active compounds of fungicides among the above-mentioned otheragricultural chemicals include, for example, (by common names, some ofwhich are still in an application stage) pyrimidinamine compounds suchas Mepanipyrim, Pyrimethanil, and Cyprodinil; azole compounds such asTriadimefon, Bitertanol, Triflumizole, Etaconazole, Propiconazole,Penconazole, Flusilazole, Myclobutanil, Cyproconazole, Terbuconazole,Hexaconazole, Furconazole-cis, Prochloraz, Metconazole, Epoxiconazole,Tetraconazole, Oxpoconazole, and Sipconazole; quinoxaline compounds suchas Quinomethionate; dithiocarbamate compounds such as Maneb, Zineb,Mancozeb, Polycarbamate, Propineb; organic chlorine compounds such asFthalide, Chlorothalonil, and Quintozene; imidazole compounds such asBenomyl, Thiophanate-Methyl, Carbendazim, and4-chloro-2-cyano-1-dimethylsulfamoyl-5-(4-methylphenyl)imidazole;pyridinamine compounds such as Fluazinam; cyanoacetamide compounds suchas Cymoxanil; phenylamide compounds such as Metalaxyl, Oxadixyl,Ofurace, Benalaxyl, Furalaxyl, and Cyprofuram; sulfenic acid compoundssuch as Dichlofluanid; copper compounds such as cupric hydroxide, andOxine Copper; isoxazole compounds such as Hydroxyisoxazole;organophosphorus compounds such as Fosetyl-Al, Tolcofos-Methyl, S-benzylO,O-diisopropylphosphorothioate, O-ethyl S,S-diphenylphosphorodithioate,and aluminumethylhydrogen phosphonate; N-halogenothioalkyl compoundssuch as Captan, Captafol, and Folpet; dicarboximide compounds such asProcymidone, Iprodione, and Vinclozolin; benzanilide compounds such asFlutolanil, Mepronil, and Zoxamide; piperazine compounds such asTriforine; pyrizine compounds such as Pyrifenox; carbinol compounds suchas Fenarimol; and Flutriafol; piperidine compounds such as Fenpropidine;morpholine compounds such as Fenpropimorph; organotin compounds such asFentin Hydroxide, and Fentin Acetate; urea compounds such as Pencycuron;cinnamic acid compounds such as Dimethomorph; phenylcarbamate compoundssuch as Diethofencarb; cyanopyrrole compounds such as Fludioxonil, andFenpiclonil; Strobilurin compounds such as Azoxystrobin,Kresoxim-Methyl, Metominofen, Trifloxystrobin, and Picoxystrobin;oxazolidinedione compounds such as Famoxadone; thiazole carboxamidecompounds such as Ethaboxam; silyl amide compounds such as Silthiopham;aminoacid amidecarbamate compounds such as Iprovalicarb; imidazolidinecompound such as Fenamidone; hydroxyanilide compounds such asFenhexamid; benzene sulfonamide compounds such as Flusulfamide;anthraquinone compounds; crotonic acid compounds; antibiotics; and othercompounds, such as Isoprothiolane, Tricyclazole, Pyroquilon,Diclomezine, Pro. benazole, Quinoxyfen, Propamocarb Hydrochloride,Spiroxamine, Chloropicrin, Dazomet, and Metam-Sodium.

Further, agricultural chemicals which may be used in admixture with orin combination with the compounds of the present invention, may, forexample, be the active ingredient compounds in the herbicides asdisclosed in Farm Chemicals Handbook (1998 edition), particularly thoseof soil treatment type.

Further, pesticides containing the compounds of the present inventionare useful as agents for controlling parasites on animals, particularlyas agents for controlling parasites in the bodies of animals, or asagents for controlling animal diseases caused by such parasites.

For example, they are effective for controlling (1) parasites parasiticon the exterior of a host animal, such as, acarus such as mange mite,mesostigmatid mites, sarcoptic mange mite (Sarcoptes scabiei),trombiculid mites, New Zealand cattle tick (Haemaphyalis longicornis)and southern cattle tick (Boophilus microplus); fleas such as cat flea(Ctenocephalides felis), dog flea (Ctenocephalides canis), northern ratflea (Nosopsyllus fasciatus), oriental rat flea (Xenopsylla cheopis) andhuman flea (Pulex irritans); sucking lice such as short-nosed cattlelouse (Haematopinus eurysternus), horse sucking louse (Haematopinusasini), sheep lice, long-nosed cattle louse (Linognathus vituli) andhead louse (Pediculus capitis); biting lice such as dog biting louse(Trichodectes canis); blood-sucking dipterous insects such as horse fly(Tabanus trigonus), biting midges (Culicoides schultzei) and blackfly(Simulium ornatum); and (2) parasites parasitic in the body of a hostanimal, such as, nematodes such as lung worms, whipworm (Trichuristrichiura), tuberous worm, gastric parasites, ascaris and filarioidea;tapeworms; flukes; and protozoa such as coccidia, malarial parasite(Plasmodium malariae), intestinal sarcocyst, Toxoplasma andcryptosporidium.

The compound of the present invention is usually formulated togetherwith a suitable vehicle into a formulation such as a powder, a granule,a parvule, a tablet, a dusting powder, a capsule, a solution or anemulsion. The suitable vehicle may be one which is commonly used as afeed additive, and it may, for example, be lactose, sucrose, glucose,starch, wheat powder, corn powder, soybean meal, degreased rice bran,calcium carbonate or other commercially available feed material.Further, the compound of the present invention can be used, togetherwith a vehicle, in combination with various vitamins, minerals, aminoacids, enzyme drugs, antifebriles, sedatives, antiphlogistics,bactericides, colorants, aromatizing agents, preservatives, etc. Thedose of the compound of the present invention varies depending upon theparasites as the object of control, the administration method, thepurpose of administration, the diseased degree, etc. However, it isusually administered as mixed in a feed in a concentration of at least0.1 ppm.

The compound of the present invention exhibits an effect for controllingparasites on animals, such as fleas, coccidia and filarioidea, by a testin accordance with the test method disclosed in e.g. JP-A-5-70350 orJP-A-11-500439.

Other preferred embodiments in the present invention are as follows.

-   (1) A phenacylamine derivative of the above formula (I) or a salt    thereof, wherein X is halogen, alkyl, haloalkyl, haloalkenyl,    haloalkynyl, alkoxy, haloalkoxy, haloalkenyloxy, haloakynyloxy,    alkylthio, haloalkylthio, haloalkenylthio, haloalkynylthio,    alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,    dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted    by Y, phenoxy which may be substituted by Y, or pyridyloxy which may    be substituted by Y.-   (2) A phenacylamine derivative of the above formula (I) or a salt    thereof, wherein X is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy,    alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,    alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro,    cyano, phenoxy which may be substituted by Y, or pyridyloxy which    may be substituted by Y.-   (3) A phenacylamine derivative of the above formula (I) or a salt    thereof, wherein A is phenyl which may be substituted by Y, R₁ and    R₂ are each alkyl, R₃ is hydrogen, X is halogen, haloalkyl,    haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl,    phenoxy which may be substituted by Y, or pyridyloxy which may be    substituted by Y, Y is halogen, alkyl, haloalkyl, haloalkoxy or    haloalkylthio, and n is an integer of from 1 to 3.

Now, the present invention will be described in further detail withreference to Examples. However, it should be understood that the presentinvention is by no means restricted to such specific Examples. Firstly,Examples for the preparation of the compounds of the present inventionwill be described.

PREPARATION EXAMPLE 1 Preparation of3,5-dichloro-N-[(4′-ethyl-1,1-dimethyl)phenacyl]benzamide (Compound No.1-84)

(1) To 360 ml of water heated to 80° C., 41 g of potassium ferricyanideand then 5.5 g of 4-ethylisobutyrophenone, were added. Then, 50 ml of28% aqueous ammonia was dropwise added over a period of 30 minutes,followed by a reaction for 16 hours at a temperature of from 85 to 90°C. The reaction mixture was extracted with ethyl acetate, followed byconcentration under reduced pressure. The residue was diluted with waterand acidified with hydrochloric acid, followed by washing with ethylacetate. The aqueous layer was neutralized with an aqueous NaOH solutionand extracted with ethyl acetate, followed by drying over anhydrousmagnesium sulfate and concentration under reduced pressure to obtain0.54 g of oily α-amino-4-ethylisobutyrophenone. The NMR spectrum data ofthis product were as follows.

¹H-NMR δ ppm (Solvent: CDCl₃/400 MHz) 1.24 (t, 3H), 1.53 (s, 6H), 2.66(q, 2H), 7.22 (d, 2H), 7.87 (d, 2H),

(2) 0.13 g of triethylamine was added to a mixture comprising 0.16 g ofα-amino-4-ethylisobutyrophenone and 4 ml of dichloroethane, and 0.18 gof 3,5-dichlorobenzoyl chloride was added under cooling with ice,followed by a reaction at room temperature for 6 hours. The reactionmixture was put into water and extracted with methylene chloride,followed by washing with water. The organic layer was dried overanhydrous sodium sulfate, followed by concentration under reducedpressure. The residue was purified by silica gel column chromatography(developing solvent: ethyl acetate/n-hexane=15/85) to obtain 0.12 g ofthe desired product having a melting point of from 176 to 177° C. TheNMR spectrum data of this product were as follows.

¹H-NMR δ ppm (Solvent: CDCl₃/400 MHz) 1.23 (t, 3H), 1.86 (s, 6H), 2.67(q, 2H), 7.24 (dd, 2H), 7.38 (s, 1H), 7.46 (d, 2H), 7.59 (d, 2H), 7.89(dd, 2H)

PREPARATION EXAMPLE 2 Preparation of2-chloro-N-[(4′-chloro-1,1-dimethyl)phenacyl]benzamide (Compound No.1-54)

(1) A mixture comprising 5.92 g of 4-chloroisobutyrophenone, 19.5 g ofN,N-dimethylhydrazin and 29.6 g of molecular sieve (3A) was reacted inan autoclave at 100° C. for 110 hours. The reaction mixture was dilutedwith methylene chloride, followed by filtration. The filtrate was driedover anhydrous magnesium sulfate, followed by concentration underreduced pressure to obtain 5.82 g of oily 4-chloroisobutyrophenonedimethylhydrazone. The NMR spectrum data of this product were asfollows.

¹H-NMR δ ppm (Solvent: CDCl₃/400 MHz) 1.05 (d, 6H), 2.31 (bs, 6H), 2.85(m, 1H), 7.14 (d, 2H), 7.32 (d, 2H)

(2) 7.82 g of methyl iodide was added to a mixture comprising 5.82 g of4-chloroisobutyrophenone dimethylhydrazone and 3.5 ml of absoluteethanol and reacted at room temperature for 15 hours. The reactionmixture was concentrated under reduced pressure, and ethyl ether wasadded to the obtained residue, followed by stirring. The precipitatedsolid was collected by filtration and washed with ethyl ether, followedby drying to obtain 10.19 g of a methyl iodide salt of4-chloroisobutyrophenone dimethylhydrazine having a melting point offrom 107 to 112° C. The NMR spectrum data of this product were asfollows.

¹H-NMR δ ppm (Solvent: CDCl₃/400 MHz) 1.13 (d, 6H), 2.83 (m, 1H), 3.58(s, 9H), 7.28 (d, 2H), 7.53 (d, 2H)

(3) A sodium methoxide solution prepared from 0.70 g of sodium and 15 mlof absolute methanol, was dropwise added at room temperature to amixture comprising 10.19 g of the methyl iodide salt of4-chloroisobutyrophenone dimethylhydrazine and 35 ml of absolutemethanol and then reacted under reflux for 3 hours. The reaction mixturewas concentrated under reduced pressure, and the residue was weaklyacidified by an addition of water and then hydrochloric acid, followedby stirring for 30 minutes. The formed solid was collected by filtrationand dried to obtain 2.46 g of α-amino-4-chloroisobutyrophenonehydrochloride (melting point: 275° C./decomposed). On the other hand,the filtrate was washed with methylene chloride and then neutralizedwith an aqueous NaOH solution. It was extracted with methylene chloride,followed by drying over anhydrous sodium sulfate and concentration underreduced pressure to obtain 0.77 g of oilyα-amino-4-chloroisobutyrophenone. The NMR spectrum data of this productwere as follows.

¹H-NMR δ ppm (Solvent: CDCl₃/400 MHz) 1.58 (s, 6H), 7.41 (d, 2H), 7.96(d, 2H)

(4) 0.47 g of triethylamine was added to a mixture comprising 0.77 g ofα-amino-4-chloroisobutyrophenone and 22 ml of dichloroethane. A mixturecomprising 0.68 g of 2-chlorobenzoyl chloride and 3 ml ofdichloroethane, was dropwise added thereto at room temperature. Aftercompletion of the dropwise addition, the mixture was reacted at the sametemperature for 15 hours. The reaction mixture was washed with water anddried over anhydrous sodium sulfate, followed by concentration underreduced pressure. The obtained residue was purified by silica gel columnchromatography (developing solvent: ethyl acetate/n-hexane=3/7) toobtain 1.05 g of the desired product having a melting point of from 99to 102° C. The NMR spectrum data of this product were as follows.

¹H-NMR δ ppm (Solvent: CDCl₃/400 MHz) 1.76 (s, 6H), 6.98 (s, 1H), 7.26(dd, 1H), 7.30-7.42 (m, 5H), 7.97 (dd, 2H)

PREPARATION EXAMPLE 3 Preparation of3,5-dichloro-N-[(4′-chloro-1,1-dimethyl)phenacyl]benzamide (Compound No.1-63)

At room temperature, 0.47 g of triethylamine and then 0.44 g of3,5-dichlorobenzoyl chloride, were added to a mixture comprising 0.49 gof α-amino-4-chloroisobutyrophenone hydrochloride and 14 ml ofdichloroethane and reacted at the same temperature for 15 hours. Thereaction mixture was washed with water and dried over anhydrous sodiumsulfate, followed by concentration under reduced pressure. To theobtained residue, n-hexane was added, and the solid was collected byfiltration and dried to obtain 0.46 g of the desired product having amelting point of from 169 to 171° C. The NMR spectrum data of thisproduct were as follows.

¹H-NMR δ ppm (Solvent: CDCl₃/400 MHz) 1.79 (s, 6H), 7.04 (s, 1H), 7.36(dd, 2H), 7.50 (s, 1H), 7.54 (d, 2H), 7.91 (dd, 2H)

PREPARATION EXAMPLE 4 Preparation of2-chloro-N-[(3′,4′-dichloro-1,1-dimethyl)phenacyl]benzamide (CompoundNo. 1-78)

At room temperature, a mixture comprising 0.215 g ofN,N′-dicyclohexylcarbodiimide and 7 ml of dichloromethane, was dropwiseadded to a mixture comprising 0.22 g ofα-amino-3,4-dichloroisobutyrophenone, 0.148 g of 2-chlorobenzoic acidand 8 ml of dichloromethane, and reacted at the same temperature for 20hours. The reaction mixture was washed with water and dried overanhydrous sodium sulfate, followed by concentration under reducedpressure. The obtained residue was purified by silica gel columnchromatography (developing solvent: ethyl acetate/n-hexane=3/7) toobtain 0.26 g of the desired product having a melting point of from 116to 120° C. The NMR spectrum data of this product were as follows.

¹H-NMR δ ppm (Solvent: CDCl₃/400 MHz) 1.76 (s, 6H), 6.89 (s, 1H),7.25-7.29 (m, 1H), 7.33-7.37 (m, 2H), 7.42-7.46 (m, 2H),7.87 (dd, 2H),8.15 (d, 2H)

PREPARATION EXAMPLE 5 Preparation ofN-methyl-N-[(1,1-dimethyl)phenacyl]-2-trifluoromethylbenzamide (CompoundNo. 1-27)

38 mg of 60% sodium hydride was added at room temperature to a mixturecomprising 0.33 g ofN-[(1,1-dimethyl)phenacyl]-2-trifluoromethylbenzamide and 5 ml oftetrahydrofuran, followed by stirring at the same temperature for 1hour. Then, 0.28 g of methyl iodide was added thereto, followed by areaction at the same temperature for 20 hours. The reaction mixture wasput into water, washed with water and dried over anhydrous sodiumsulfate. The residue obtained by concentration under reduced pressure,was purified by silica gel column chromatography (developing solvent:ethyl acetate/n-hexane=3/7) to obtain 0.30 g of a desired product havinga melting point of from 149 to 150° C. The NMR spectrum data of thisproduct were as follows.

¹H-NMR δ ppm (Solvent: CDCl₃/400 MHz) 1.64 (s, 3H), 1.67 (s, 3H), 2.92(s, 3H), 6.65 (dd, 1H), 7.40-7.44 (m, 4H), 7.47-7.49 (m, 1H), 7.59 (dd,1H), 7.92 (dd, 2H)

Now, typical examples of the compound of the present invention of theabove formula (I) will be given in Tables 1 to 4. These compounds can beprepared in accordance with the above Preparation Examples or by theabove-described various processes for the production of the compounds ofthe present invention.

Abbreviations used in the Tables are as follows.

Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group,Ph: phenyl group, allyl: ally group, X-1:

X-2:

X-3:

X-4: F₂C═CH—, X-5: F₂C═CHCH₂—, X-6: Cl₂C═CHCH₂O—, X-7: F₂C═CHCH₂CH₂—,X-8: F₂BrC(CH₂)₃—, X-9: IC≡CCH₂—, X-10: (CH₃)₃CC≡CCH₂—, X-11: HC≡CCH₂—,X-12: IC≡CCH₂—

In the Tables, 4-[X-1] indicates that X-1 is substituted at the4-position. The same applies to other expressions.

TABLE 1

Physical Compound properties No. R₁ R₂ R₃ X Y (mp ° C.) 1-1 Me Me H H2-F 110-111 1-2 Me Et H H 2-F 1-3 —(CH₂)₂— H H 2-F 1-4 Me Me H H 2,6-F₂109-113 1-5 Me Me H H 2-Cl 128-131 1-6 Me Et H H 2-Cl 1-7 Me Me COMe H2-Cl 205-209 1-8 —(CH₂)₂— H H 2-Cl 1-9 —(CH₂)₄— H H 2-Cl 1-10 Me Me H H3-Cl 159-161 1-11 Me Me H H 4-Cl 155-160 1-12 Me Me H H 2,3-Cl₂ 122-1261-13 Me Me H H 2,4-Cl₂ 144-147 1-14 Me Me H H 2,5-Cl₂ 190-191 1-15 Me MeH H 2,6-Cl₂ 160-163 1-16 Me Me H H 3,5-Cl₂ 160-161 1-17 Me Me H H 2-Br149-150 1-18 Me Me H H 2-Me 171-172 1-19 Me Me H H 4-Me 182-185 1-20 MeMe H H 3,5-Me₂ 157-159 1-21 Me Me H H 2-Et 1-22 Me Me H H 4-Et 194-1951-23 Me Me H H 4-tert-Bu 180-181 1-24 Me Me H H 2-CF₃ 158-161 1-25—(CH₂)₂— H H 2-CF₃ 1-26 —(CH₂)₅— H H 2-CF₃ 178-180 1-27 Me Me Me H 2-CF₃149-150 1-28 Me Me H H 4-CF₃ 184-186 1-29 Me Me H H 2-OMe 118-121 1-30Me Me H H 4-OMe 171-175 1-31 Me Me H H 2-SMe 127-132 1-32 Me Me H H4-SMe 185-187 1-33 Me Me H H 4-SOMe 1-34 Me Me H H 2-SO₂Me 177-180 1-35Me Me H H 4-SO₂Me 189-191 1-36 Me Me H H 4-SO₂CF₃ 1-37 Me Me H H4-SO₂NMe₂ 1-38 Me Me H H 2-NO₂ 184-187 1-39 Me Me H H 4-NO₂ 1-40 Me Me HH 4-CN 1-41 Me Me H 4-F H 150-152 1-42 Me Me H 4-F 2-F 78-81 1-43 Me MeH 4-F 2-Cl 152-155 1-44 Me Me H 4-F 2-CF₃ 151-154 1-45 Me Me H 2-Cl HOil 1-46 Me Me H 2-Cl 2-Cl 85-87 1-47 Me Me H 3-Cl H 136-138 1-48 Me MeH 3-Cl 2-Cl 168-169 1-49 Me Me H 4-Cl H 161-162 1-50 Me Me H 4-Cl 2-F164-167 1-51 Me Et H 4-Cl 2-F 93-95 1-52 —(CH₂)₂— H 4-Cl 2-F 1-53 Me MeH 4-Cl 2,6-F₂ 146-148 1-54 Me Me H 4-Cl 2-Cl  99-102 1-55 Me Me Na 4-Cl2-Cl 270/decomposed 1-56 —(CH₂)₄— H 4-Cl 2-Cl 1-57 Me Me H 4-Cl 3-Cl145-147 1-58 Me Me H 4-Cl 4-Cl 191-195 1-59 Me Me H 4-Cl 2,3-Cl₂ 129-1311-60 Me Me H 4-Cl 2,4-Cl₂ 152-153 1-61 Me Me H 4-Cl 2,5-Cl₂ 1-62 Me Me H4-Cl 2,6-Cl₂ 1-63 Me Me H 4-Cl 3,5-Cl₂ 169-171 1-64 Me Me H 4-Cl 2-Br149-151 1-65 Me Me H 4-Cl 2-Me 160-163 1-66 Me Me H 4-Cl 3-Me 1-67 Me MeH 4-Cl 4-Me 1-68 Me Me H 4-Cl 3,5-Me₂ 1-69 Me Me H 4-Cl 2-Et 1-70 Me MeH 4-Cl 2-CF₃ 95-97 1-71 Me Et H 4-Cl 2-CF₃ 147-149 1-72 —(CH₂)₅— H 4-Cl2-CF₃ 1-73 Me Me H 4-Cl 4-CF₃ 1-74 Me Me H 4-Cl 2-OMe 1-75 Me Me H3,4-Cl₂ H 171-173 1-76 Me Me H 3,4-Cl₂ 2-CF₃ 1-77 Me Me H 3,4-Cl₂ 2-F114-116 1-78 Me Me H 3,4-Cl₂ 2-Cl 116-120 1-79 Me Me H 3,5-Cl₂ 2-Cl146-149 1-80 Me Me H 4-Me H 181-182 1-81 Me Me H 4-Me 2-Cl 141-143 1-82Me Me H 4-Et H 172-174 1-83 Me Me H 4-Et 2-Cl 116-118 1-84 Me Me H 4-Et3,5-Cl₂ 176-177 1-85 Me Me H 4-Et 3,5-Me₂ 179-181 1-86 Me Me H 4-tert-BuH 1-87 Me Me H 4-tert-Bu 2-F 136-139 1-88 Me Me H 4-tert-Bu 2-Cl 172-1761-89 Me Me H 4-tert-Bu 2-CF₃ 150-153 1-90 Me Me H 4-CF₃ H 178-179 1-91Me Me H 4-CF₃ 2-Cl 127-129 1-92 Me Me H 4-OMe H 156-157 1-93 Me Me H4-OMe 2-Cl 112-114 1-94 Me Me H 4-OCHF₂ H 1-95 Me Me H 4-OCHF₂ 2-Cl65-70 1-96 Me Me H 4-OCF₃ H 1-97 Me Me H 4-OCF₃ 2-Cl 1-98 Me Me H 4-SMeH 158-160 1-99 Me Me H 4-SMe 2-Cl 128-129 1-100 Me Me H 4-SOMe H 1-101Me Me H 4-SO₂Me H 222-225 1-102 Me Me H 4-SO₂CF₃ H 1-103 Me Me H4-SO₂NMe₂ H 1-104 Me Me H 4-NO₂ H 1-105 Me Me H 4-NO₂ 2-F 1-106 Me Me H4-NO₂ 2-Cl 1-107 Me Me H 4-NO₂ 2-CF₃ 1-108 Me Me H 4-CN H 1-109 Me Me H4-CN 2-Cl 1-110 Me Me H 4-CN 2-CF₃ 1-111 Me Me H H 2-CN 1-112 Me Me H4-Cl 2-CN 1-113 —(CH₂)₂— H 3,5-Cl₂ 4-Et 1-114 Me Me H H 2-OCF₃ 1-115 MeMe H 4-Cl 2-OCF₃ 1-116 —(CH₂)₂— H 2-Cl 3,5-Me₂ 1-117 Me Me CO₂Me 3,4-Cl₂H 1-118 Me Me CH₂OEt 4-NO₂ 4-Cl 1-119 Me Me H 4-[X-1] 3,5-Cl₂ 1-120 MeMe H 4-[X-2] 2-Cl 1-121 Me Me H 4-[X-3] H 1-122 —(CH₂)₅— H H 2-F 154-1571-123 —(CH₂)₅— H H 2-Cl 155-161 1-124 —(CH₂)₅— H H 2,6-F₂ 178-180 1-125Me Me H H 2,4-F₂ 140-143 1-126 Me Me H 3-F 2,6-F₂ 142-144 1-127 Me Me H4-F 2,3-F₂ 119-122 1-128 Me Me H 4-F 2,6-F₂ 141-143 1-129 Me Me H 3,4-F₂H 148-150 1-130 Me Me H 3,4-F₂ 2-F 101-104 1-131 Me Me H 3,4-F₂ 2-Cl 97-100 1-132 Me Me H 3,4-F₂ 2-CF₃ 157-161 1-133 Me Me H 3,4-F₂ 2,6-F₂141-145 1-134 Me Me H 2-Cl 2,6-F₂ Oil 1-135 Me Me H 3-Cl 2,6-F₂ Oil1-136 Me Me H 4-Cl 2-NO₂ 174-178 1-137 Me Me H 4-Cl 2-Cl-4-NO₂ 141-1451-138 Me Me H 4-Cl 2-Cl-4-F 126-130 1-139 Me Me H 4-Cl 2,3-F₂ 116-1191-140 Me Me H 4-Cl 2,4-F₂  98-100 1-141 Me Me H 4-Cl 2,5-F₂ 107-1091-142 Me Me H 4-Cl 2-Cl-6-F 105-110 1-143 Me Me H 2,4-Cl₂ 2,6-F₂ 100-1031-144 Me Me H 3,5-Cl₂ H 159-161 1-145 Me Me H 3,5-Cl₂ 2-Cl 199-204 1-146Me Me H 3,5-Cl₂ 2,6-F₂ 156-158 1-147 Me Me H 3,4-Cl₂ 2,6-F₂ 140-1451-148 Me Et H 4-Cl H 158-160 1-149 Me Et H 4-Cl 2-Cl 127-129 1-150 Me EtH 4-Cl 2,4-F₂ 84-86 1-151 Me Et H 4-Cl 2,6-F₂ 115-117 1-152 Et Et H 4-Cl2-Cl 158-160 1-153 Et Et H 4-Cl 2-CF₂ 150-152 1-154 Et Et H 4-Cl 2,6-F₂138-142 1-155 Me Me H 4-Br 2-Cl 50-56 1-156 Me Me H 4-Br 2-CF₂ 134-1401-157 Me Me H 4-Br 2,6-F₂ 128-133 1-158 Me Me H 4-Br 2-F 109-112 1-159Me Me H 4-Br 2,3-F₂ 116-118 1-160 Me Me H 4-I 2-F 122-126 1-161 Me Me H4-I 2-CF₃ 165-168 1-162 Me Me H 4-I 2,6-F₂ 102-110 1-163 Me Me H 4-Me2,6-F₂ 126-128 1-164 Me Me H 4-Et 2,6-F₂ Oil 1-165 Me Me H 4-Pr 2,6-F₂Oil 1-166 Me Me H 4-CF₃ 2,6-F₂ 102-110 1-167 Me Me H 4-CF₃ 2-F 91-931-168 Me Me H 4-OMe 2,6-F₂ Oil 1-169 Me Me H 4-OEt 2,6-F₂ Oil 1-170 MeMe H 4-OPr 2,6-F₂ Oil 1-171 Me Me H 4-OCHF₂ 2-F 74-77 1-172 Me Me H4-OCHF₂ 2,6-F₂ 90-94 1-173 Me Me H 4-OCH₂CF₃ 2-F 94-96 1-174 Me Me H4-OCH₂CF₃ 2,6-F₂ 139-147 1-175 Me Me H 4-OCF₂CHF₂ 2-F 129-131 1-176 MeMe H 4-OCF₂CHF₂ 2-Cl 135-138 1-177 Me Me H 4-OCF₂CHF₂ 2,6-F₂ 115-1191-178 Me Me H 4-OCF₂CHF₂ 2-CF₃ 120-125 1-179 Me Me H 4-OCH₂CF₂CF₃ 2-F88-91 1-180 Me Me H 4-OCH₂CF₂CF₃ 2,6-F₂ 128-130 1-181 Me Me H4-OCF₂CHFCF₃ 2-F 1-182 Me Me H 4-OCF₂CHFCF₃ 2,6-F₂ 1-183 Me Me H 4-allyl2-F 1-184 Me Me H 4-allyl 2,6-F₂ 1-185 Me Me H 4-[-4] 2-F 1-186 Me Me H4-[-4] 2,6-F₂ 1-187 Me Me H 4-[-5] 2-F 1-188 Me Me H 4-[-5] 2,6-F₂ 1-189Me Me H 4-[-6] 2-F Oil 1-190 Me Me H 4-[-6] 2,6-F₂ Oil 1-191 Me Me H4-O-[-7] 2-F 1-192 Me Me H 4-O-[-7] 2,6-F₂ 1-193 Me Me H 4-O-[-8] 2-F1-194 Me Me H 4-O-[-8] 2,6-F₂ 1-195 Me Me H 4-S-[-7] 2-F 1-196 Me Me H4-S-[-7] 2,6-F₂ 1-197 Me Me H 4-S-[-8] 2-F 1-198 Me Me H 4-S-[-8] 2,6-F₂1-199 Me Me H 4-[X-11] 2-F 1-200 Me Me H 4-[X-11] 2,6-F₂ 1-201 Me Me H4-[X-9] 2-F 1-202 Me Me H 4-[X-9] 2,6-F₂ 1-203 Me Me H 4-[X-10] 2-F1-204 Me Me H 4-[X-10] 2,6-F₂ 1-205 Me Me H 4-Ph 2-F 155-160 1-206 Me MeH 4-Ph 2,6-F₂ 177-179 1-207 Me Me H 4-OPh 2-F Oil 1-208 Me Me H 4-OPh2,6-F₂ Oil 1-209 Me Me H 4-OPh 2-CF₃ 143-146 1-210 Me Me H 4-OCH₂Ph2,6-F₂ 166-171 1-211 Me Me H 4-[X-2] 2,6-F₂ 75-80 1-212 Me Me H 4-SMe2,6-F₂ Oil 1-213 Me Me H 4-SO₂Me 2,6-F₂ 176-178 1-214 Me Me H 4-O-allyl2-F 1-215 Me Me H 4-O-allyl 2,6-F₂ 1-216 Me Me H 4-S-allyl 2-F 1-217 MeMe H 4-S-allyl 2,6-F₂ 1-218 Me Me H 4-O-[X-11] 2-F 1-219 Me Me H4-O-[X-11] 2,6-F₂ 1-220 Me Me H 4-O-[X-12] 2-F 1-221 Me Me H 4-O-[X-12]2,6-F₂ 1-222 Me Me H 4-S-[X-11] 2-F 1-223 Me Me H 4-S-[X-11] 2,6-F₂1-224 Me Me H 4-S-[X-12] 2-F 1-225 Me Me H 4-S-[X-12] 2,6-F₂ 1-226 Me MeH 4-tert-Bu 2,6-F₂ 104-109

TABLE 2

Physical Compound properties No. R₁ R₂ R₃ X Y (mp ° C.) 2-1  Me Me H H H2-2  Me Me H H 2-Cl 213-215 2-3  Me Me H H 4-Cl 2-4  Me Me H H 2-CF₃2-5  Me Me H H 4-CF₃ 152-154 2-6  Me Me H 2-Cl 2-F 2-7  Me Me Me 2-Cl2-Me 2-8  Me Me H 3-Cl H 2-9  Me Me H 3-Cl 2-Cl 2-10 Me Me H 4-Cl H 2-11Me Me H 4-Cl 2-CF₃ 2-12 Et Et H 4-Cl H 2-13 Me Me H 4-Cl 2-Cl 2-14 Me MeH 4-Cl H 2-15 Me Me H 4-OCF₃ 2-Cl 2-16 Me Me H 4-SMe H 2-17 Me Me H4-SMe 2-Cl 2-18 Me Me H 4-SOMe H 2-19 Me Me H 4-SO₂Me H 2-20 Me Me H4-SO₂CF₃ H 2-21 Me Me H 4-SO₂NMe₂ H 2-22 Me Me H 4-NO₂ H 2-23 Me Me H4-NO₂ 2-Cl 2-24 Me Et H 4-CN H 2-25 Me Me H 4-CN 2-Cl

TABLE 3

Physical Compound properties No. R₁ R₂ R₃ X Y₁ Y₂ (mp ° C.) 3-1  Me Me HH H Cl 3-2  Me Me H H H CF₃ 108-110 3-3  Me Me H H Cl Cl 3-4  Me Me H HCl CF₃ 3-5  Me Me H H Me Cl 3-6  Me Me H H Me CF₃ 3-7  Me Me H H Cl Me103-105 3-8  Me Me H H CF₃ Me 3-9  Me Me H H Me Me 3-10 Me Me COMe H ClCl 3-11 Me Me H 4-F Cl Me 3-12 Me Me H 2-Cl Cl Cl 3-13 Me Me H 3-Cl ClCF₃ 3-14 Me Me H 4-Cl Cl H 3-15 Me Me H 4-Cl Cl Me 3-16 Me Me H 4-Cl ClCl 3-17 Me Me H 4-Cl Cl CF₃ 3-18 Et Et H 4-Cl Cl Cl 3-19 Me Me H 3,5-Cl₂Cl Cl 3-20 Me Me H 4-Me H Cl 3-21 Me Me H 3,5-Me₂ Cl CF₃ 3-22 Me Me H4-tert-Bu H Cl 3-23 Me Me H 4-tert-Bu Cl Cl 3-24 Me Me H 4-OMe Cl Cl3-25 Me Me H 3,5-(OMe)₂ Cl Cl

TABLE 4

Physical Compound properties No. R₁ R₂ R₃ X A (mp ° C.) 4-1  Me Me H HMe 4-2  Me Me H H Et 4-3  Me Me H H iso-Pr 4-4  Me Me H H tert-Bu125-127 4-5  Me Me H H Cyclopropyl 150-152 4-6  Me Me H 2-Cl tert-Bu4-7  Me Me H 2-Cl Cyclohexyl 4-8  Me Me H 3-Cl tert-Bu 4-9  Me Me H 3-ClCyclopentyl 4-10 Me Me Me 4-Cl Me 4-11 Me Me H 4-Cl Et 4-12 Me Et H 4-Cliso-Pr 4-13 Me Me H 4-Cl tert-Bu 4-14 Me Me H 4-Cl Cyclohexyl 4-15 Me MeH 4-Me tert-Bu 4-16 Me Me H 4-OMe tert-Bu 4-17 Me Me H 3,4-(OMe)₂tert-Bu 4-18 Me Me H 2-F-4-CF₃ tert-Bu 4-19 Me Me H 4-OCHF₂ tert-Bu 4-20Me Me H 4-SMe tert-Bu 4-21 Me Me H 4-SMe Cyclopentyl 4-22 Et Et H 4-NO₂tert-Bu 4-23 Me Me H 4-NO₂ Cyclohexyl 4-24 Me Me H 4-CN tert-Bu 4-25 MeMe H 4-CN Cyclohexyl

Now, Test Examples will be described.

TEST EXAMPLE 1 Test on Southern Root-knot Nematode

(Meloidgyne incognita)

To 300 ml of the soil contaminated by southern root-knot nematode, 7 mlof a chemical solution having the concentration of the compound of thepresent invention adjusted to be 1600 ppm, was poured, followed bymixing so that the compound was uniformly dispersed. The treated soilwas put into a pot (diameter: 9 cm, height: 8 cm), and then a tomatoseedling in 2-leaf stage was transplanted and placed in a greenhouse.After three to four weeks from the transplantation of the tomato, theroot knot index was determined based on the following standards.

Degree of formation of root Root knot index knots 0 No knot was formed 1Knots were formed to a slight degree 2 Knots were formed to a moderatedegree 3 Knots were formed to a heavy degree 4 Knots were formed to theheaviest degree

As a result, the above-mentioned compounds Nos. 1-1, 1-4,1-5, 1-17,1-18, 1-19, 1-24, 1-27, 1-28, 1-31, 1-38, 1-49, 1-50, 1-51, 1-54, 1-64,1-65, 1-70, 1-77, 1-83, 1-84, 1-93, 1-95, 1-125, 1-126, 1-127, 1-128,1-130, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-138, 1-139, 1-140,1-141, 1-142, 1-143, 1-147, 1-151, 1-155, 1-156, 1-157, 1-158, 1-159,1-160, 1-161, 1-162, 1-163, 1-164, 1-166, 1-167, 1-168, 1-169, 1-171,1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-211,1-212, 1-213 and 2-2 showed high controlling effects at a level of aroot knot index of not more than 1.

TEST EXAMPLE 2 Test on Oocysts

Eimeria tenella of wild type is infected to chicks to obtain freshimmature oocysts, which are then exposed to a solution having apredetermined concentration of the compound of the present invention for10 or 30 minutes. The exposed immature oocysts are subjected tocentrifugal separation, and after removing the supernatant, a 2%potassium bichromate aqueous solution is added, followed by sporulationat 25° C. for 4 days, whereby good oosyst controlling effects areconfirmed.

TEST EXAMPLE 3 Test on Dog Filarioidea

To a dog subcutaneously infected with dog filarioidea (Dirofilariaimmitis), the compound of the present invention is orally administered.At the time of an autopsy after 200 days from the infection, the numberof adults of dog filarioidea parasitic to the lung or heart of thetreated animal is investigated, whereby good effects for controlling dogfilarioidea is confirmed.

Now, formulation Examples will be described.

FORMULATION EXAMPLE 1

(1) Compound of the present invention 20 parts by weight (2) Clay 72parts by weight (3) Sodium lignin sulfonate  8 parts by weight

The above components are uniformly mixed to obtain a wettable powder.

FORMULATION EXAMPLE 2

(1) Compound of the present invention  5 parts by weight (2) Talc 95parts by weight

The above components are uniformly mixed to obtain a dust.

FORMULATION EXAMPLE 3

(1) Compound of the present invention 20 parts by weight (2)N,N′-dimethylacetamide 20 parts by weight (3) Polyoxyethylenealkylphenylether 10 parts by weight (4) Xylene 50 parts by weight

The above components are uniformly mixed and dissolved to obtain anemulsifiable concentrate.

FORMULATION EXAMPLE 4

(1) Clay 68 parts by weight (2) Sodium lignin sulfonate  2 parts byweight (3) Polyoxyethylenealkylaryl sulfate  5 parts by weight (4) Finesilica powder 25 parts by weight

A mixture of the above components is mixed with compound of the presentinvention in a weight ratio of 4:1 to obtain a wettable powder.

FORMULATION EXAMPLE 5

(1) Compound of the present invention   50 parts by weight (2) Oxylatedpolyalkylphenyl   2 parts by weight phosphate-triethanolamine (3)Silicone  0.2 part by weight (4) Water 47.8 parts by weight

The above components are uniformly mixed and pulverized to obtain a baseliquid, and

(5) Sodium polycarboxylate 5 parts by weight

(6) Anhydrous sodium sulfate 42.8 parts by weight

are added, and the mixture is uniformly mixed and dried to obtainwater-dispersible granules.

FORMULATION EXAMPLE 6

(1) Compound of the present invention 5 parts by weight (2)Polyoxyethyleneoctylphenyl ether 1 part by weight (3) polyoxyethylenephosphoric 0.1 part by weight acid ester (4) Granular calcium carbonate93.9 parts by weight

The above components (1) to (3) are preliminarily uniformly mixed anddiluted with a proper amount of acetone, and then the mixture is sprayedonto the component (4), and acetone is removed to obtain granules.

FORMULATION EXAMPLE 7

(1) Compound of the present invention  2.5 parts by weight (2)N-methyl-2-pyrrolidone  2.5 parts by weight (3) Soybean oil 95.0 partsby weight

The above components are uniformly mixed and dissolved to obtain anultra low volume formulation.

1. A phenacylamine derivative of the formula (I) or a salt thereof:

wherein A is alkyl, cycloalkyl, phenyl which may be substituted-by Y,pyridyl which may be substituted by Y, or pyrazolyl which may besubstituted by Y, R₁, and R₂ are each alkyl, or R₁ and R₂ may togetherform an unsubstituted 3- to 6-membered saturated carbocycle, R₃ ishydrogen, alkyl, alkoxyalkyl, alkylthioalkyl or COR₄, R₄ is alkyl oralkoxy, X is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl,haloalkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy,haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio,alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano,phenyl which may be substituted by Y, phenoxy which may be substitutedby Y, benzyloxy which may be substituted by Y, or pyridyloxy which maybe substituted by Y, Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy,alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro or cyano,n is an integer of from 0 to 5, and when n is 2 or more, a plurality ofX may be the same or different, provided that the following compoundsare excluded (1) a compound wherein A is unsubstituted phenyl, R₁ and R₂are each methyl or together form a 6-membered saturated carbocycle, R₃is hydrogen, and n is 0, and (2) a compound wherein A is methyl ortertiary butyl, R₁, and R₂ are each methyl, R₃ is hydrogen and n is 0.2. The phenacylamine derivative or a salt thereof according to claim 1,wherein X is halogen, alkyl, haloalkyl, haloalkenyl, haloalkynyl,alkoxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, alkylthio,haloalkylthio, haloalkenylthio, haloalkynylthio, alkylsulfinyl,haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted byY, phenoxy which may be substituted by Y, or pyridyloxy which may besubstituted by Y.
 3. The phenacylamine derivative or a salt thereofaccording to claim 1, wherein X is halogen, alkyl, haloalkyl, alkoxy,haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano,phenoxy which may be substituted by Y, or pyridyloxy which may besubstituted by Y.
 4. The phenacylamine derivative or a salt thereofaccording to claim 1, wherein A is phenyl which may be substituted by Y,R₁, and R₂ are each alkyl, R₃ is hydrogen, X is halogen, haloalkyl,haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, phenoxywhich may be substituted by Y, or pyridyloxy which may be substituted byY, Y is halogen, alkyl, haloalkyl, haloalkoxy or haloalkylthio, and n isan integer of from 1 to
 3. 5. A pesticide which contains thephenacylamine derivative or a salt thereof as defined in claim 1, as anactive ingredient.
 6. An agricultural and horticultural pesticide whichcontains the phenacylamine derivative or a salt thereof as defined inclaim 1, as an active ingredient.
 7. An insecticide, miticide ornematicide which contains the phenacylamine derivative or a salt thereofas defined in claim 1, as an active ingredient.
 8. A nematicide whichcontains the phenacylamine derivative or a salt thereof as defined inclaim 1, as an active ingredient.
 9. An agent for controlling parasiteson animals, which contains the phenacylamine derivative or a saltthereof as defined in claim 1, as an active ingredient.
 10. An agent forcontrolling parasites in the interior of animals, which contains thephenacylamine derivative or a salt thereof as defined in claim 1, as anactive ingredient.
 11. An agent for controlling animal diseases causedby parasites, which contains the phenacylamine derivative or a saltthereof as defined in claim 1, as an active ingredient.
 12. A method forcontrolling a pest, which comprises applying an effective amount of thephenacylamine derivative or a salt thereof as defined in claim 1 to thepest.
 13. The phenacylamine derivative or a salt thereof according toclaim 1, wherein said derivative or salt thereof is isolated.
 14. Thephenacylamine derivative or a salt thereof according to claim 1, whereinsaid derivative or salt thereof is chemically synthesized.
 15. Thephenacylamine derivative or a salt thereof according to claim 1, whereinsaid derivative or salt thereof is purified.
 16. The phenacylaminederivative or a salt thereof according to claim 1, wherein R₁ and R₂together form a —(CH₂)₂—; —(CH₂)₄—; or —(CH₂)₅-group.
 17. Thephenacylamine derivative or a salt thereof according to claim 1, whereinR₁ and R₂ are each independently selected from the group consisting ofmethyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl and hexyl.18. A process for producing a phenacylamine derivative of the formula(I) or a salt thereof:

wherein A is alkyl, cycloalkyl, phenyl which may be substituted by Y,pyridyl which may be substituted by Y, or pyrazolyl which may besubstituted by Y, R₁ and R₂ are each alkyl, or R₁ and R₂ may togetherform a 3- to 6-membered saturated carbocycle, R₃ is hydrogen, alkyl,alkoxyalkyl, alkylthioalkyl or COR₄, R₄ is alkyl or alkoxy, X ishalogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkenyl, haloalkynyl,alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy,haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkynylthio,alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano,phenyl which may be substituted by Y, phenoxy which may be substitutedby Y, benzyloxy which may be substituted by Y, or pyridyloxy which maybe substituted by Y, Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy,alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro or cyano,n is an integer of from 0 to 5, and when n is 2 or more, a plurality ofX may be the same or different, provided that a case where A isunsubstituted phenyl, R₁ and R₂ are each methyl or together form a6-membered saturated carbocycle, R₃ is hydrogen, and n is 0, isexcluded, which comprises (A) reacting a compound of the formula (II):

wherein R₁, R₂, X and n are as defined above, with a compound of theformula (III):A-COZ  (III) wherein A is as defined above, and Z is hydroxyl, alkoxy orhalogen, or (B) reacting a compound of the formula (I-1)

wherein A, R₁, R₂, X and n are as defined above, with a compound of theformula (IV):R₃′-W  (IV) wherein R₃′ is alkyl, alkoxyalkyl, alkylthioalkyl or COR₄,R₄ is as defined above, and W is halogen.
 19. The process according toclaim 18, wherein A is phenyl which may be substituted by Y, R₁ and R₂are each alkyl, R₃ is hydrogen, X is halogen, haloalkyl, haloalkoxy,haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, phenoxy which maybe substituted by Y, or pyridyloxy which may be substituted by Y, Y ishalogen, alkyl, haloalkyl, haloalkoxy or haloalkylthio, and n is aninteger of from 1 to
 3. 20. The process according to claim 18, wherein Xis halogen, alkyl, haloalkyl, haloalkynyl, haloalkynyl, alkoxy,haloalkoxy, haloalkenyloxy, haloalkynyloxy, alkylthio, haloalkylthio,haloalkenylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano,phenyl which may be substituted by Y, phenoxy which may be substitutedby Y, or pyridyloxy which may be substituted by Y.
 21. The processaccording to claim 18, wherein X is halogen, alkyl, haloalkyl, alkoxy,haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano,phenoxy which may be substituted by Y, or pyridyloxy which may besubstituted by Y.